Maximum quantity allowed is 999
Please select the quantity
TCI Practical Example: The Synthesis of α-Aminoamide Catalyzed by a Visible Light Photoredox Catalyst
We are proud to present the synthesis of an α-aminoamide from N,N-dimethylaniline and p-toluenesulfonylmethyl isocyanide by using Ir[(ppy)2(bpy)]PF6 as a visible light photoredox catalyst.
Used Chemicals
Procedure
N,N-Dimethylaniline (0.18 g, 1.5 mmol, 1.0 eq.), TosMIC (0.439 g, 2.25 mmol, 1.5 eq.), Ir[(ppy)2(bpy)]PF6(12 mg, 0.015 mmol, 1.0 mol%), ion-exchanged water (0.27 mL, 15 mmol, 10 eq.) were dissolved in acetonitrile (10 mL) at room temperature under nitrogen gas atmosphere. The mixture was placed at a distance of 2-3 cm from the Blue LED lamps. The orange solution was stirred at room temperature under visible light irradiation. After 2 days of irradiation, the solvent was removed in vacuo and the resulting residue was purified by column chromatography on silica gel (hexane:ethyl acetate = 9:1 - 1:1 - 0:1) to give compound 1 as a light brown solid (131 mg, 26% yield).
Experimenter’s Comments
- Acetonitrile was degassed with nitrogen for 1 hour before use.
- Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W x 2.
- The reaction mixture was monitored by 1H NMR and TLC (hexane:ethyl acetate = 1:1, Rf = 0.23).
Analytical Data
Compound 1
1H NMR (400 MHz, CDCl3); δ 7.72 (d, J = 8.2 Hz, 2H), 7.34-7.27 (m, 5H), 6.89 (t, J = 6.9 Hz, 1H), 6.67 (d, J = 8.7 Hz, 2H), 4.69 (d, J = 6.9 Hz, 2H), 3.75 (s, 2H), 2.99 (s, 3H), 2.45 (s, 3H).
13C NMR (101 MHz, CDCl3); δ 170.3, 148.9, 145.6, 133.6, 129.9, 129.4, 128.8, 119.2, 113.3, 59.8, 58.5, 40.0, 21.8.
Lead Reference
- Visible Light Photoredox-Catalyzed Multicomponent Reactions
Other Reference
- (review) A Retrosynthetic Approach for Photocatalysis